Ethyl Bromide → HCID 57055631, compound

HRID 1980627Notes

Reaction equation

HRID 1980627 reaction equation
[CH2:1]([Li])[CH3:2].C(Br)C.[Li].[CH3:8][O:9][C:10]1[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=1[OH:21])=[O:13].[Cl-].[NH4+]>O1CCCC1.CCOCC>[CH3:8][O:9][C:10]1[CH:25]=[CH:24][CH:23]=[CH:22][C:11]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=1[OH:21])([OH:13])[CH2:1][CH3:2]

Participants

8

Reactant 5

HCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 12721024(2,4-Dihydroxyphenyl)(2-methoxyphenyl)methanoneHCID 178506846HCID 178506846, compound

Product 1

HCID 57055631HCID 57055631, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To an ethyl lithium solution prepared from 29.4 g. of ethyl bromide and 3.7 g. of lithium in 33o ml. of dry ether, under argon atmosphere, which is cooled to -10° C., a solution of 11 g. of 2-methoxy-2',4'-dihydroxy-benzophenone in 60 ml. of dry tetrahydrofurane is added dropwise, taking care that the temperature does not exceed -5° C. Thereafter the reaction mixture is stirred at 0° C. for 30 minutes and then at room temperature for two hours. The reaction mixture is decomposed with a 10% aqueous ammonium chloride solution, the phases are separated, and the aqueous phase is extracted with ether. The combined ethereal phases are washed to neutral with water, dried over anhydrous magnesium sulfate, filtered, and the solvent is distilled off in vacuo, after decoloring with activated carbon. Crystallization of the solid residue from a mixture of n-hexane and ethyl acetate yields 8.3 g. of the named compound, melting at 141° to 142° C.

Workup

  1. customdoes not exceed -5° C
  2. waitat room temperature for two hours
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted with ether
  5. washThe combined ethereal phases are washed to neutral with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. distillationthe solvent is distilled off in vacuo
  9. customCrystallization of the solid residue
  10. additionfrom a mixture of n-hexane and ethyl acetate
  11. customyields 8.3 g

Sources & evidence

ORD record
ord-3141c4bfd75646879e603608595b5d64
Source dataset
uspto-grants-1985_04
Patent number
US04510338

Reaction notes

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